tert-butyl (1S)-1-benzyl-2-hydroxypropylcarbamate → HCID 57112585, compound

HRID 47738Notes

Reaction equation

HRID 47738 reaction equation
[CH2:1]([C@H:8]([NH:12]C(=O)OC(C)(C)C)[CH:9]([OH:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1>[NH2:12][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]([OH:11])[CH3:10]

Participants

3

Reactant 1

HCID 14212468tert-butyl (1S)-1-benzyl-2-hydroxypropylcarbamate

Product 1

HCID 57112585HCID 57112585, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
20 °C

Procedure

The process is performed as in Example 3, starting with 17.6 g of tert-butyl (1S)-1-benzyl-2-hydroxypropylcarbamate in 145 cm3 of dioxane and 61 cm3 of 6.5N hydrochloric dioxane, stirring for 16 hours at a temperature in the region of 20° C. After an identical work-up, 9.56 g of (3S)-3-amino-4-phenyl-2-butanol are obtained in the form of an orange-colored oil as a mixture of the two diastereoisomers (80/20). (Rf=0.25 in a 40/5/0.5 by volume mixture of dichloromethane/methanol/aqueous ammonia, on a Merck 60F254R silica plate).

Sources & evidence

ORD record
ord-c910825e49104cc0a04810caaba9ee26
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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