HCID 2756026, compound → tert-butyl (1S)-1-benzyl-2-hydroxypropylcarbamate

HRID 1280638Notes

Reaction equation

HRID 1280638 reaction equation
[CH2:1]([C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH2:1]([C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]([OH:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2756026HCID 2756026, compoundHCID 4311764Sodium borohydride

Product 1

HCID 14212468tert-butyl (1S)-1-benzyl-2-hydroxypropylcarbamateYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The process is performed as in Example 3, starting with 2.66 g of tert-butyl (1S)-1-benzyl-2-oxopropylcarbamate in 25 cm3 of ethanol, with 0.58 g of sodium borohydride. After 4 h 30 min at a temperature in the region of 20° C., the reaction mixture is worked up in an identical manner. 2.7 g of tert-butyl (1S)-1-benzyl-2-hydroxypropylcarbamate are obtained in the form of a white solid melting at 125° C., as a mixture of the two diastereoisomers (70/30).

Sources & evidence

ORD record
ord-c1b24a860dad4fb283c292a502f2eafb
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Reaction notes

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