Sodium borohydride → Fmoc-Orn(Z)-ol

HRID 9709Notes

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-0254ce23dea8486095efb817b0675e5b
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091314B2

Reaction notes

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