Sodium borohydride → Fmoc-Orn(Z)-ol

HRID 1160600Notes

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-c7a4db4b3c8947358e133dce176b599e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816489B2

Reaction notes

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