Sodium borohydride → HCID 14723166, compound

HRID 2247884Notes

Reaction equation

[BH4-].[Na+].[CH2:3]([N:5]([CH2:31][CH3:32])[C:6]([NH:8][C@H:9]1[CH2:23][C@H:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[NH:16][C:15]=3[C:25]([CH3:27])=[CH2:26])[N:11]([CH2:28][CH2:29][CH3:30])[CH2:10]1)=[O:7])[CH3:4]>>[CH2:31]([N:5]([CH2:3][CH3:4])[C:6]([NH:8][C@H:9]1[CH2:23][C@H:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[NH:16][C:15]=3[CH:25]([CH3:26])[CH3:27])[N:11]([CH2:28][CH2:29][CH3:30])[CH2:10]1)=[O:7])[CH3:32]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 14723163HCID 14723163, compound

Product 1

HCID 14723166HCID 14723166, compound

Procedure

In the reduction with sodium borohydride a mixture of the desired compound and 1,1-diethyl-3-(2-isopropenyl- 6-n-propyl-8α-ergolinyl)-urea) was produced. Therefore the raw mixture was further reduced with Na/NH3 (see example 12). Yield after crystallization (ethyl acetate): 28%, [α]D +17.6° (c=0.5 in chloroform).

Sources & evidence

ORD record: ord-3a5e9c75643748cb865975096fbe12cd
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05037832

Reaction notes

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