Bromoacetonitrile → 3-Hydroxy-1-pyrrolidineacetonitrile

HRID 226245Notes

Reaction equation

HRID 226245 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.Br[CH2:8][C:9]#[N:10]>C1COCC1>[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:8][C:9]#[N:10])[CH2:3]1

Participants

4

Reactant 2

HCID 11534BromoacetonitrileHCID 982104-Hydroxypyrrolidine

Product 1

HCID 534019273-Hydroxy-1-pyrrolidineacetonitrileYield 64,545.699%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method follows that of S3 using 3-hydroxypyrrolidine (15 g, 0.172 mol), BrCH2CN (22.67 g, 0.189 mmol) and dry THF (60 mL). The title-compound was yielded as a straw-coloured oil (15.39 g, 71%) after flash chromatography using CH2Cl2/CH3OH (9:1) as eluent. δH (250 MHz; CDCl3); 1.9-2.25 (m, 2H, 2×ring-H), 2.3 (m, 1H, ring-H), 2.65 (d, OH), 2.85-3.05 (m, 3H, 3×ring-H), 3.95 (d, 2H, NCH2CN) and 4.2 (m, 1H, CH2CHOH); FAB MS, m/z (M+H)+ 127.

Sources & evidence

ORD record
ord-95c1337e4b6144deaae42514e26a9d3c
Source dataset
uspto-grants-2009_07
Patent number
US07557215B2

Reaction notes

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