Formaldehyde → HCID 67071538, compound

HRID 874269Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([C:18](OC(C)(C)C)=O)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:29].C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([CH3:18])[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:29]

Participants

Reactant 3

HCID 712Formaldehyde

HCID 5049666Sodium triacetoxyborohydride

HCID 67071624HCID 67071624, compound2×

Product 1

HCID 67071538HCID 67071538, compound

Procedure

(±)-(E)-3-[1′-Methyl-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid methyl ester was synthesized starting from the hydrochloride salt of (±)-(E)-3-[4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid methyl ester (500 mg, 1.43 mmol, Intermediate 3), according to the procedure for preparation of Example 23, Step A, using aqueous 37% formaldehyde solution (0.127 ml, 1.71 mmol), and NaBH(OAc)3 (461 mg, 2.14 mmol) giving a yellow solid (374 mg).

Workup

customaccording to the procedure for preparation of Example 23, Step A

Sources & evidence

ORD record: ord-f41b43ef76a8478b9d40c01cc8c82d6f
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980877B2

Reaction notes

Loading…