5alpha-Cholestan-3-one → 3beta-(3-Methanesulfonyloxy-1-Azetidinyl)-5alpha-Cholestane

HRID 2052347Notes

Reaction equation

HRID 2052347 reaction equation
[CH3:1][S:2]([O:5][CH:6]1[CH2:9][NH:8][CH2:7]1)(=[O:4])=[O:3].[CH3:10][CH:11]([CH2:13][CH2:14][CH2:15][C@H:16]([C@@H:18]1[C@:35]2([CH3:36])[C@H:21]([C@H:22]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C@H:25]([CH2:26][C:27](=O)[CH2:28][CH2:29]2)[CH2:24][CH2:23]3)[CH2:20][CH2:19]1)[CH3:17])[CH3:12].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C.O>[CH3:1][S:2]([O:5][CH:6]1[CH2:9][N:8]([C@H:27]2[CH2:28][CH2:29][C@@:30]3([CH3:31])[C@@H:25]([CH2:24][CH2:23][C@@H:22]4[C@@H:32]3[CH2:33][CH2:34][C@@:35]3([CH3:36])[C@H:21]4[CH2:20][CH2:19][C@@H:18]3[C@H:16]([CH3:17])[CH2:15][CH2:14][CH2:13][CH:11]([CH3:10])[CH3:12])[CH2:26]2)[CH2:7]1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 921285alpha-Cholestan-3-oneHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 7330605Azetidin-3-yl methanesulfonate

Product 1

HCID 867367923beta-(3-Methanesulfonyloxy-1-Azetidinyl)-5alpha-Cholestane

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 3.50 g of the mesylate salt of 3-methanesulfonyloxyazetidine (m.p. 111.5°-113° C. dec.) and 5.46 g of 5α-cholestan-3-one in 100 ml of anhydrous methanol maintained at room temperature under a nitrogen atmosphere add 1.74 g sodium cyanoborohydride portionwise over a 20 minute period. Stir for 30 minutes at room temperature, pour into 600 ml water, add to the mixture 100 ml 1.1 M aqueous sodium bicarbonate and extract three times with ethyl ether. Combine the ether extracts, dry over 3 A molecular sieves and remove solvent in vacuo to give a mixture of α- and β-mesylates. Chromatography of this mixture on 150 g Stahl-type silica using ethyl acetate affords the pure title product (slower-moving component), m.p., 135.5° C. dec., [α]D26 =+12.1° (CHCl3, 0.4%).

Workup

  1. extractionextract three times with ethyl ether
  2. customdry over 3 A molecular sieves
  3. customremove solvent in vacuo
  4. customto give

Sources & evidence

ORD record
ord-c577c36d93c54775ad491386c248e874
Source dataset
uspto-grants-1980_01
Patent number
US04183923

Reaction notes

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