Benzaldehyde → HCID 67071573, compound

HRID 874239Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:17](=[CH:18][CH:19]=1)[O:16][C:11]1([CH2:15][CH2:14][NH:13][CH2:12]1)[CH2:10][C:9]2=[O:20].[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:17](=[CH:18][CH:19]=1)[O:16][C:11]1([CH2:15][CH2:14][N:13]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:12]1)[CH2:10][C:9]2=[O:20]

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 5049666Sodium triacetoxyborohydride

HCID 67071421HCID 67071421, compound

Product 1

HCID 67071573HCID 67071573, compound

Procedure

(−)-(E)-3-[4-Oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (110 mg, 0.38 mmol) was treated with benzaldehyde and NaBH(OAc)3 according to the procedure used for Example 2, Step A to give (+)-(E)-3-[1′benzyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (45 mg).

Sources & evidence

ORD record: ord-4263e9362adf49f79cf0caaad4b37986
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980877B2

Reaction notes

Loading…