1-Butanol → HCID 178448267, compound

HRID 64388Notes

Reaction equation

HRID 64388 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@@H:5]3[C@@H:22]([C@@:23]4([CH3:29])[CH2:24][CH2:25][C@H:26]([OH:28])[CH2:27][C:2]124)[CH2:21][CH2:20][C@@:19]1([CH3:30])[C@H:6]3[CH2:7][CH2:8][C@:9]1([OH:31])[C@H:10]([CH3:18])[CH2:11][CH2:12][C@@H:13]([CH3:17])[CH:14]([CH3:16])[CH3:15].[NH2:32][CH2:33][CH2:34][C:35]1[N:39]=[CH:38][NH:37][CH:36]=1.C(O)CCC>COC(C)(C)C>[OH:1][C@:2]12[CH2:27][C@@H:26]([OH:28])[CH2:25][CH2:24][C@:23]1([CH3:29])[C@@H:22]1[C@H:5]([C@H:6]3[C@:19]([CH3:30])([CH2:20][CH2:21]1)[C@@:9]([OH:31])([C@H:10]([CH3:18])[CH2:11][CH2:12][C@@H:13]([CH3:17])[CH:14]([CH3:15])[CH3:16])[CH2:8][CH2:7]3)[CH2:4][C@H:3]2[NH:32][CH2:33][CH2:34][C:35]1[N:39]=[CH:38][NH:37][CH:36]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 1317372175,6alpha-Epoxicampestane-3beta,17-diolHCID 178419017HCID 178419017, compound

Product 1

HCID 178448267HCID 178448267, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

5,6α-epoxicampestane-3β,17-diol (6.8 g, 22.1 mmol, 1 eq) and histamine (4.9 g, 44.1 mmol, 2 eq) were charged in a round-bottomed flask equipped with a magnetic stirrer bar. 1-Butanol (70 ml, 5 vol) was added and the mixture heated to reflux for 40 h. The reaction mixture was cooled at r.t., diluted with methyl-tertbutyl-ether (5 vol) and washed with water (5 vol) and with brine (5 vol). The organic layer was passed through a silica pad (40 g) eluted with methyl-tertbutyl-ether (3 vol) then 10% Methanol/ethyl acetate (60 vol). Fractions of interest were pooled and the solvent was removed under reduced pressure to give (5α-Hydroxy-6β-[2-(1H-imidazol-4-yl)-ethylamino]-campestane-3β,17-diol) as a white solid (5.7 g, 49%). In same conditions, use of ethanol as solvent (40 vol) and Ca(OTf)2 as catalyst gave a 13% yield.

Workup

  1. customequipped with a magnetic stirrer bar
  2. temperaturethe mixture heated
  3. temperatureto reflux for 40 h
  4. washwashed with water (5 vol) and with brine (5 vol)
  5. washeluted with methyl-tertbutyl-ether (3 vol)
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ed2c1e2e276f457784b655718ff6f119
Source dataset
uspto-grants-2016_09
Patent number
US09447141B2

Reaction notes

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