(S)-TERT-BUTYL (1-(3-FLUOROPHENYL)-3-HYDROXYPROPAN-2-YL)CARBAMATE synthesis

2synthesis methods

Product Name:(S)-TERT-BUTYL (1-(3-FLUOROPHENYL)-3-HYDROXYPROPAN-2-YL)CARBAMATE
CAS Number:944470-56-8
Molecular formula:C14H20FNO3
Molecular Weight:269.31

114873-01-7
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(S)-TERT-BUTYL (1-(3-FLUOROPHENYL)-3-HYDROXYPROPAN-2-YL)CARBAMATE

944470-56-8
25 suppliers
$314.00/1g

Yield:944470-56-8 74%

Reaction Conditions:

Stage #1: N-Boc-3-fluoro-L-phenylalaninewith borane-THF in tetrahydrofuran at 0; for 12 h;
Stage #2: with methanol;acetic acid in tetrahydrofuran;

Steps:

1.a

To a solution of N-{[(1 ,1-dimethylethyl)oxy]carbonyl}-3-fluoro-L-phenylalanine (10 g, 35.3 mmol) in THF (200 ml.) at 0 ⁰C stirred was added BH₃-THF (88 ml_, 88 mmol-1 M in THF). After 12h, the reaction was quenched with AcOH:MeOH (8:50, 58 ml.) and partitioned between saturated aqueous NaHCO₃ and DCM. The aqueous phase was then extracted several times with DCM. The combined organic fractions were concentrated and the residue passed through a pad of silica gel (hexanes/EtOAc, 1 :1 ) to afford the product compound (7.0 g, 74%) as a white solid: LCMS (ES) m/e 270 (M+H)⁺.

References:

WO2009/158371,2009,A1 Location in patent:Page/Page column 33

Carbamic acid, N-[(1S)-2-(3-fluorophenyl)-1-formylethyl]-, 1,1-dimethylethyl ester

848444-61-1
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944470-56-8
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$314.00/1g

References