Ethyl Acetate → HCID 59122958, compound

HRID 489216Notes

Reaction equation

HRID 489216 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[C@H:10](N)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N(C1C=C(OC)C(OC)=C(OC)C=1)=C=[O:30].CCOC(C)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([OH:30])[C@H:11]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl Acetate2×HCID 5177665-Isocyanato-1,2,3-trimethoxybenzeneHCID 59122957HCID 59122957, compound

Product 1

HCID 59122958HCID 59122958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure C, (±)-trans-3-amino-4-[4-(4-chlorobenzyl)piperidin-1-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (394 mg, ˜0.9 mmol) and 5-isocyanato-1,2,3-trimethoxybenzene (250 mg, 1.2 mmol) were coupled in CH2Cl2 (6.0 mL) at 0° C. for 1 h. Chromatography of the crude product with 1:1 hexanes:EtOAc to 100% EtOAc gave the product (445 mg, 77% from (±)-trans-3-[4-(4-chlorobenzyl)piperidin-1-yl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester) as a white solid: mp 99.0-102.5° C.; IR 3371 (br), 2932, 1655, 1607, 1552, 1507 cm−1; 1H NMR δ 1.17-1.80 (m, 14H), 2.18 (m, 2H), 2.48 (d, J=7.0 Hz, 2H), 2.95-3.51 (m, 8H), 3.81 (m, 9H), 4.32 (br, 1H), 5.30 (br, 1H), 6.61 (s, 2H), 7.02 (m, 2H), 7.20 (m, 2H); MS m/z 603.2 (M+H)+.

Sources & evidence

ORD record
ord-669acc1010674f819dc68bdf22f61870
Source dataset
uspto-grants-2005_12
Patent number
US06977265B2

Reaction notes

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