Sodium borohydride → Fmoc-Orn(Z)-ol

HRID 968964Notes

Reaction equation

[NH:1]([C:20]([O:22][CH2:23][CH:24]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[C@H:2]([C:17](O)=[O:18])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[BH4-].[Na+]>>[NH:1]([C:20]([O:22][CH2:23][CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]2[C:36]1=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:21])[C@H:2]([CH2:17][OH:18])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 14999635Fmoc-orn(Z)-OH

Product 1

HCID 131725891Fmoc-Orn(Z)-ol

Procedure

Commercially available Fmoc-Orn(Z) was converted to the alcohol by reduction of its mixed anhydride with sodium borohydride. After crystallization from EtOAc, the compound was thereafter used without further purification.

Workup

customAfter crystallization from EtOAc
customthe compound was thereafter used without further purification

Sources & evidence

ORD record: ord-e2c373e4952142c9b296285f1e7d26c7
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304181B2

Reaction notes

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