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Sodium Hydroxide → 2,2-diphenyl-2-[(3R)-pyrrolidin-3-yl]acetamide

HRID 2253905
Notes
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Reaction equation

HRID 2253905 reaction equation
[C:1]([C:3]([C@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2].[OH-:21].[Na+]>S(=O)(=O)(O)O.O>[C:1]([C:3]([C@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:21])[NH2:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11010789(R)-2,2-diphenyl-2-(pyrrolidin-3-yl)acetonitrile

Product 1

HCID 115074252,2-diphenyl-2-[(3R)-pyrrolidin-3-yl]acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

3-(R)-(-)-(1-cyano-1,1-diphenylmethyl)pyrrolidine (9.2 g-see Preparation 9(B)) was dissolved in 95% sulphuric acid (80 ml) and the mixture was heated at 80° C. for 4 hours and then at 90° C. for 1 hour. Ice (1 kg) was added and the mixture was basified (pH 12) by the addition of a cold solution of sodium hydroxide (120 g) in water (100 ml). The mixture was extracted with dichloromethane (4×100 ml) and the combined extracts were dried (MgSO4) then concentrated in vacuo to give a foam which was purified by column chromatography on alumina eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a foam, yield, 4.5 g, [α]D25 +16.9° (c 1.0, CH2Cl2).

Workup

  1. extractionThe mixture was extracted with dichloromethane (4×100 ml)
  2. dry with materialthe combined extracts were dried (MgSO4)
  3. concentrationthen concentrated in vacuo
  4. customto give a foam which
  5. customwas purified by column chromatography on alumina eluting with dichloromethane
  6. additioncontaining methanol (0% up to 10%)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fcbe88ad64f94d1ba80f9374b06dd5ce
Source dataset
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05233053

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes