Hydrochloric Acid → 1-{1-[(2S)-2-pyrrolidinyl]cyclopropyl}pyrrolidine hydrochloride

HRID 1366644Notes

Reaction equation

HRID 1366644 reaction equation
C1(C[N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]2([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:15][CH2:14]2)C=CC=CC=1.[ClH:21]>CO>[ClH:21].[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66936125(2S)-1-(phenylmethyl)-2-[1-(1-pyrrolidinyl)cyclopropyl]pyrrolidine

Product 1

HCID 669364481-{1-[(2S)-2-pyrrolidinyl]cyclopropyl}pyrrolidine hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S)-1-(Phenylmethyl)-2-[1-(1-pyrrolidinyl)cyclopropyl]pyrrolidine (1.083 g, 4.00 mmol) was dissolved in a mixture of MeOH (30 mL) and 1N HCl (8.8 mL), degassed and placed under argon. 10% Pd/C (325 mg) was added, and the contents were thoroughly degassed and placed under a hydrogen balloon for 2 h. The contents were then degassed, and the Pd/C was removed by filtration through a fiberglass filter, washing with MeOH. The filtrate was concentrated in vacuo to provide pure 1-{1-[(2S)-2-pyrrolidinyl]cyclopropyl}pyrrolidine hydrochloride (0.978 g, >99%). LCMS: (M+H)+: 181.2.

Workup

  1. customdegassed
  2. addition10% Pd/C (325 mg) was added
  3. customthe contents were thoroughly degassed
  4. customfor 2 h
  5. customThe contents were then degassed
  6. customthe Pd/C was removed by filtration through a fiberglass
  7. filtrationfilter
  8. washwashing with MeOH
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ea4fedfc5d404634b69809888c25929d
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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