1-Butanol → 5alpha-Hydroxy-6beta-(3-propylamino)-cholest-7-en-3beta-ol

HRID 64391

Reaction equation

HRID 64391 reaction equation
[O:1]1[C@H:3]2[CH:4]=[C:5]3[C@@H:21]([C@@:22]4([CH3:28])[CH2:23][CH2:24][C@H:25]([OH:27])[CH2:26][C:2]124)[CH2:20][CH2:19][C@@:18]1([CH3:29])[C@H:6]3[CH2:7][CH2:8][C@@H:9]1[C@H:10]([CH3:17])CCCC(C)C.[NH2:30][CH2:31][CH2:32][C:33]1C2C(=CC=CC=2)NC=1.[CH2:42](O)[CH2:43]CC.CO[C:49]([CH3:52])([CH3:51])[CH3:50]>>[OH:1][C@:2]12[CH2:26][C@@H:25]([OH:27])[CH2:24][CH2:23][C@:22]1([CH3:28])[C@@H:21]1[C:5]([C@H:6]3[C@:18]([CH3:29])([CH2:19][CH2:20]1)[C@@H:9]([C@H:10]([CH3:17])[CH2:42][CH2:43][CH2:50][CH:49]([CH3:52])[CH3:51])[CH2:8][CH2:7]3)=[CH:4][C@H:3]2[NH:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 1150TryptamineHCID 15413tert-Butyl methyl etherHCID 872266475,6alpha-Epoxicholest-7-en-3beta-ol

Product 1

HCID 1176426835alpha-Hydroxy-6beta-(3-propylamino)-cholest-7-en-3beta-olYield 59%

Procedure

5,6α-epoxicholest-7-en-3β-ol (8.9 g, 22.1 mmol, 1 eq) and tryptamine (7.1 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-(3-propylamino)-cholest-7-en-3β-ol as a white solid (7.3 g, 59%). In same conditions, use of ethanol as solvent (40 vol) and Ca(OTf)2 as catalyst gave a 23% 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-37cb1dbd7f284525ba54028279f43338
Source dataset
uspto-grants-2016_09
Patent number
US09447141B2

Linked notes

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