Water → HCID 22795184, compound

HRID 1973685Notes

Reaction equation

HRID 1973685 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 53847304HCID 53847304, compound

Product 1

HCID 22795184HCID 22795184, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2) A solution of cis-2-(3-methoxyphenyl)-1-pyrrolidinocyclohexane (2.5g) in dichloromethane was added cautiously to an ice-cold solution of boron tribromide (3 ml) in dichloromethane (15 ml). The mixture was set aside at room temperature for 18 hours and was hydrolysed with water. The aqueous layer was collected, made alkaline with ammonia and extracted with ether. The ether extracts were washed, dried (Na2SO4) and evaporated. The residue was crystallised from aqueous ethanol to give cis-2-(3-hydroxyphenyl)-1-pyrrolidinocyclohexane (2.0g), m.p. 125° to 127° C, identical to (b)(1) above.

Workup

  1. customThe aqueous layer was collected
  2. extractionextracted with ether
  3. washThe ether extracts were washed
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was crystallised from aqueous ethanol

Sources & evidence

ORD record
ord-c8ed6634821f47539eb22fa33da6407a
Source dataset
uspto-grants-1976_12
Patent number
US03998843

Reaction notes

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