Sodium Hydroxide → (3R)-α,α-Diphenyl-3-pyrrolidineacetamide

HRID 1742706Notes

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]

Participants

Conditions

Temperature: 80 °C

Procedure

3 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]25D +16 9° (c 1.0, CH2Cl2).

Workup

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

Sources & evidence

ORD record: ord-d777a0fc5271446fac7d74c8ac542a01
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05340831

Reaction notes

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