Formic Acid → HCID 86736868, compound

HRID 1701436Notes

Reaction equation

HRID 1701436 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]([O:11][C@H:12]1[CH2:31][C@@:30]2([CH3:32])[C@@H:23]([CH2:24][CH2:25][C@@H:26]2[C:27](=[O:29])[CH3:28])[C@H:22]2[C@H:13]1[C@:14]1([CH3:34])[C@@H:19]([CH2:20][CH2:21]2)[CH2:18][C@@H:17]([OH:33])[CH2:16][CH2:15]1)=[O:10])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:54](O)=[O:55].CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:1]([N:4]([CH2:8][C:9]([O:11][C@H:12]1[CH2:31][C@@:30]2([CH3:32])[C@@H:23]([CH2:24][CH2:25][C@@H:26]2[C:27](=[O:29])[CH3:28])[C@H:22]2[C@H:13]1[C@:14]1([CH3:34])[C@@H:19]([CH2:20][CH2:21]2)[CH2:18][C@H:17]([O:33][CH:54]=[O:55])[CH2:16][CH2:15]1)=[O:10])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 70585544HCID 70585544, compound

Product 1

HCID 86736868HCID 86736868, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11β-N,N-Dipropylaminoacetoxy-3β-hydroxy-5α-pregnan-20-one (110 mg) was stirred with triphenylphosphine (364 mg) and formic acid (0.1 ml) in tetrahydrofuran (5 ml.) and diethylazodicarboxylate (240 mg) added. Further reagent (5 drops) was added until a good yellow colour persisted. After 16 hours the mixture was concentrated and filtered through silica gel (20 g) in ethyl acetate: petroleum ether (1:1). Evaporation of the eluate gave a residue which was purified by preparative TLC (ethyl acetate: petroleum ether (1:1)) to give 11β-N,N-dipropylaminoacetoxy-3α-formyloxy-5α-pregnan-20-one (30 mg), [α]D +73°.

Workup

  1. additionadded
  2. concentrationAfter 16 hours the mixture was concentrated
  3. filtrationfiltered through silica gel (20 g) in ethyl acetate: petroleum ether (1:1)
  4. customEvaporation of the eluate
  5. customgave a residue which
  6. customwas purified by preparative TLC (ethyl acetate: petroleum ether (1:1))

Sources & evidence

ORD record
ord-ca08812235f647d1883c974aa4fd210a
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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