1-Bromopentadecane → (3S,4S)-3-(N-Benzyloxycarbonylamino)-4-nonadecanol

HRID 722824Notes

Reaction equation

HRID 722824 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:15][CH3:16])[CH:13]=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C@@H:13]([OH:14])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])[CH2:15][CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 123941-BromopentadecaneHCID 22883909Benzyl [(1S)-1-formylpropyl]carbamate

Product 1

HCID 58743303(3S,4S)-3-(N-Benzyloxycarbonylamino)-4-nonadecanol

Procedure

According to the method of Example 26, from aldehyde 8 (680 mg, 3.1 mmol) and 1-bromopentadecane (6.55 g, 22.5 mmol), alcohol 92 was obtained as a colorless oil (800 mg, 60% yield).

Sources & evidence

ORD record
ord-90752718a4cc4b39bd377002275346d6
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Reaction notes

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