Formaldehyde → HCID 67071443, compound

HRID 874255Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][CH2:14][N:13]([C:17](OC(C)(C)C)=O)[CH2:12]1)[CH2:10][C:9]2=[O:28].C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][CH2:14][N:13]([CH3:17])[CH2:12]1)[CH2:10][C:9]2=[O:28]

Participants

Reactant 3

HCID 712Formaldehyde

HCID 5049666Sodium triacetoxyborohydride

HCID 67071461HCID 67071461, compound

Product 1

HCID 67071443HCID 67071443, compoundYield 96.3%

Procedure

(±)-(E)-3-[1′-Methyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester was synthesized starting from Intermediate 2 (800 mg, 2.37 mmol), according to the procedure for preparation of Example 13, Step A, using aqueous 37% formaldehyde solution (0.212 ml, 2.85 mmol), and NaBH(OAc)3 (754 mg, 3.55 mmol) giving (±)-(E)-3-[1′-methyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester as yellow solid (720 mg).

Workup

custom(±)-(E)-3-[1′-Methyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester was synthesized
customaccording to the procedure for preparation of Example 13, Step A

Sources & evidence

ORD record: ord-7fc865e6ef714f548348b6c65b184997
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980877B2

Reaction notes

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