p-Toluenesulfonic acid → HCID 69905541, compound

HRID 1837123Notes

Reaction equation

HRID 1837123 reaction equation
[CH:1]([O:4][C@H:5]1[CH2:22][C@@:21]2([CH3:23])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=O)[CH2:7][C@@H:6]1[OH:25])([CH3:3])[CH3:2].[BH3-]C#N.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1.S1(CCCC1)(=O)=O>O.CN(C=O)C>[CH:1]([O:4][C@H:5]1[CH2:22][C@@:21]2([CH3:23])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][CH2:15]2)[CH2:7][C@@H:6]1[OH:25])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acid2×HCID 31347SulfolaneHCID 5003444Sodium cyanoborohydride2×HCID 699057232beta-Isopropoxy-3alpha-hydroxy-5alpha-androstan-17-one

Product 1

HCID 69905541HCID 69905541, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 2β-isopropoxy-3α-hydroxy-5α-androstan-17-one tosylhydazone (300 mg), NaBH3CN (144 mg) and p-toluenesulfonic acid (30 mg) was added DMF and sulfolane (1:1, 3 mL) and the mixture obtained was heated to 110° C. for 3 h. Then additional amount of NaBH3CN (144 mg) and p-toluenesulfonic acid (30 mg) was added and it was heated for another hour. Water was then added and the mixture was extracted with EtOAc (2×45 mL). The combined extracts were dried over Na2SO4 and the crude product obtained by removal of the solvent was purified by flash chromatography over silica gel to yield the pure 2β-isopropoxy-3α-hydroxy-5α-androstane (37 mg); TLC Rf (EtOAc:hexane 1:9)=0.17.

Workup

  1. customthe mixture obtained
  2. temperatureit was heated for another hour
  3. extractionthe mixture was extracted with EtOAc (2×45 mL)
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. customthe crude product obtained by removal of the solvent
  6. customwas purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-44bd2b5b0a5149d3a31d299bc45f0d79
Source dataset
uspto-grants-2004_08
Patent number
US06780853B1

Reaction notes

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