tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate → rel-1,1-Dimethylethyl (3R,4S)-3-(4-fluorophenyl)-4-hydroxy-1-pyrrolidinecarboxylate

HRID 2377029Notes

Reaction equation

HRID 2377029 reaction equation
[CH:1]12[O:6][CH:5]1[CH2:4][N:3]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2]2.[F:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1>>[C:10]([O:9][C:7]([N:3]1[CH2:2][C@@H:1]([C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)[C@H:5]([OH:6])[CH2:4]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylateHCID 178418676HCID 178418676, compound

Product 1

HCID 86610906rel-1,1-Dimethylethyl (3R,4S)-3-(4-fluorophenyl)-4-hydroxy-1-pyrrolidinecarboxylate

Procedure

The title compound was prepared from tert-butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate and 4-fluorophenylmagnesium bromide according to the procedure for Example 1, step A. 1H-NMR (CDCl3): δ: 1.49 (s, 9H), 3.2-3.4 (m, 3H), 3.50 (m, 1H), 3.7-3.95 (m, 2H), 4.32 (q, 1H, 5 Hz), 7.05 (t, 2H), 7.23 (m, 2H) ppm.

Sources & evidence

ORD record
ord-db84ee6227514d46b3db5cae146c3f8f
Source dataset
uspto-grants-2008_12
Patent number
US07468437B2

Reaction notes

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