tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate → HCID 66605688, compound

HRID 2410777Notes

Reaction equation

HRID 2410777 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:12]=[C:11]([C:21]([NH2:23])=[O:22])[C:7]=3[NH:8][C:9]=2[CH:10]=1.O[C@H:25]1[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]1>>[C:15]1([C:13]2[CH:12]=[C:11]([C:21]([NH2:23])=[O:22])[C:7]3[NH:8][C:9]4[CH:10]=[C:2]([O:1][C@@H:25]5[CH2:29][CH2:28][NH:27][CH2:26]5)[CH:3]=[CH:4][C:5]=4[C:6]=3[N:14]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylateHCID 178513536HCID 178513536, compound

Product 1

HCID 66605688HCID 66605688, compound

Procedure

This was similarly prepared from 7-hydroxy-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxamide and (5)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate. MS (ESI) m/z 373.1 (M+H). 1H NMR (500 MHz, MeOD) δ ppm 8.28 (1H, d, J=8.85 Hz), 8.16 (1H, s), 8.11 (2H, d, J=7.02 Hz), 7.54 (2H, t, J=7.63 Hz), 7.44 (1H, t, J=7.32 Hz), 7.17 (1H, d, J=2.14 Hz), 6.92 (1H, dd, J=8.85, 2.14 Hz), 5.05-5.13 (1H, m), 3.14-3.23 (3H, m), 3.00 (1H, ddd, J=11.22, 8.32, 4.88 Hz), 2.16-2.27 (1H, m), 2.05-2.15 (1H, m).

Sources & evidence

ORD record
ord-25f05562b2914930923e65099ab1cff3
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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