(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine → HCID 89682761, compound

HRID 2278242Notes

Reaction equation

HRID 2278242 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4](F)[CH:3]=1.[NH:11]1[CH2:15][CH2:14][C@@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12]1>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N:11]2[CH2:15][CH2:14][C@@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:12]2)[CH:3]=1

Participants

3

Reactant 2

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 27249084-Chloro-2-fluorobenzaldehyde

Product 1

HCID 89682761HCID 89682761, compound

Procedure

The title compound was prepared from 4-chloro-2-fluoro-benzaldehyde and (R)-tert-butyl pyrrolidin-3-ylcarbamate as described in Example 70, Step 1 (30.0 mg, 81%). 1H NMR 400 MHz (CDCl3) δ 9.98 (s, 1H), 7.63 (d, J=8.3 Hz, 1H), 6.89-6.79 (m, 2H), 4.77 (s, 1H), 3.57 (dd, J=10.7, 6.0 Hz, 2H), 3.34 (s, 1H), 3.25-3.18 (m, 1H), 2.28 (td, J=12.9, 7.0 Hz, 1H), 2.00 (td, J=12.5, 6.4 Hz, 2H), 1.46 (s, 9H). LCMS (ESI, an/z): 325 [M+H]+.

Sources & evidence

ORD record
ord-1f93d4af4c0c4f88ab043beabae1fba8
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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