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Piperidine → 3beta,17beta-Diacetoxy-13-(2-chlorovinyl)-10-methyl-gon-5-ene

HRID 972270
Notes
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Reaction equation

HRID 972270 reaction equation
[C:1]([O:4][C@H:5]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:20]2[CH2:19][CH2:18][C@@:15]2([CH:16]=O)[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:25][C:26](=[O:28])[CH3:27])[CH2:6]1)(=[O:3])[CH3:2].[Cl-].[Cl:30][CH2:31][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.N1CCCCC1.C([Li])CCC>O1CCCC1.CCCCCC>[C:1]([O:4][C@H:5]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C:7](=[CH:8][CH2:9][C@H:10]3[C@H:11]4[C@@:15]([CH:16]=[CH:31][Cl:30])([C@@H:14]([O:25][C:26](=[O:28])[CH3:27])[CH2:13][CH2:12]4)[CH2:18][CH2:19][C@@H:20]32)[CH2:6]1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8082PiperidineHCID 197823(Chloromethyl)triphenylphosphonium chlorideHCID 54229142HCID 54229142, compoundHCID 178418339Butyllithium

Product 1

HCID 867351243beta,17beta-Diacetoxy-13-(2-chlorovinyl)-10-methyl-gon-5-ene

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 8058HexaneSolvent

Procedure

A solution of 2.92 g of 3β,17β-diacetoxy-androst-5-en-18-al in 30 ml of tetrahydrofurane is added dropwise to a solution of a Wittig reagent prepared from 7.83 g of chloromethyl-triphenyl-phosphonium chloride, 144 ml of tetrahydrofurane, 2.23 ml of piperidine and 11.25 ml of a 1.56 molar solution of butyl-lithium in hexane and the mixture is allowed to react for 40 minutes at room temperature and is worked up as indicated in Example 1. On purification by chromatography, as also indicated in Example 1A, this gives the cis and trans isomers of 3β,17β-diacetoxy-13-(2-chlorovinyl)-10-methyl-gon-5-ene in a ratio of 1:3. The cis isomer crystallises from methylene chloride/hexane and then melts at 161°-162° C; [α]D25 = -70° (in chloroform); the trans isomer crystallises from methylene chloride/hexane, melting point 155°-156° C, [α]D25 = -42° (in chloroform).

Workup

  1. customto react for 40 minutes at room temperature
  2. customOn purification by chromatography

Sources & evidence

ORD record
ord-8e30718bb4294aec8649a2daa6b17208
Source dataset
uspto-grants-1977_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04052421

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes