Phenylacetaldehyde → HCID 67071692, compound

HRID 874281Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:27])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:23](=[CH:24][CH:25]=1)[O:22][C:11]1([CH2:14][N:13]([C:15](OC(C)(C)C)=O)[CH2:12]1)[CH2:10][C:9]2=[O:26].[C:28]1([CH2:34]C=O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][O:2][C:3](=[O:27])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:23](=[CH:24][CH:25]=1)[O:22][C:11]1([CH2:14][N:13]([CH2:15][CH2:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:12]1)[CH2:10][C:9]2=[O:26]

Participants

Reactant 3

HCID 998Phenylacetaldehyde

HCID 5049666Sodium triacetoxyborohydride

HCID 67071422HCID 67071422, compound

Product 1

HCID 67071692HCID 67071692, compound

Procedure

(E)-3-[1′-(2-Phenyl-ethyl)-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl]acrylic acid methyl ester was synthesized starting from Intermediate 4 (350 mg, 1.13 mmol), according to the procedure described in Example 31, Step A, using phenylacetaldehyde (0.25 ml, 2.3 mmol) and NaBH(OAc)3 (360 mg, 1.69 mmol). The product was obtained as a yellow solid (378 mg).

Sources & evidence

ORD record: ord-4c07f15de6db4e9b8f22f90d983542b2
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980877B2

Reaction notes

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