Lithium borohydride → tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate

HRID 620150Notes

Reaction equation

HRID 620150 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[BH4-].[Li+].CO.C(Cl)(Cl)Cl>COCCOC>[C:9]([O:8][C:6]([NH:5][C@H:4]([CH2:3][OH:2])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:7])([CH3:11])([CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 4148881Lithium borohydrideHCID 9882138Boc-L-phenylalanine methyl esterHCID 21584188Chloroform methanol

Product 1

HCID 2733675tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamateYield 89%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

This compound was prepared in 89% yield from the ester 4d (11.2 g, 40 mmol) by reduction with lithium borohydride in dry DME analogous to the method described earlier1,2. TLC Rf 0.50 (eluent MeOH/CHCl3, 7/93). 1H NMR (CDCl3) δ 1.40 (s, 9H, t-Bu), 2.00-2.53 (m, 1H, OH), 2,83 (d, J=5.4 Hz, 2H, CH2Ph), 3.33-4.08 (m, 3H, CH2OH, CHCH2), 4.48-4.94 (br d, 1H, NH), 7.22 (s, 5H, Ph). CI MS, m/e 252 (M+ +1).

Sources & evidence

ORD record
ord-86f75fe393ab42aea1de0f003f124fb6
Source dataset
uspto-grants-1989_04
Patent number
US04820712

Reaction notes

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