Acetic Acid → HCID 67071514, compound

HRID 874322Notes

Reaction equation

HRID 874322 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].CC(O)=O.[CH3:32][N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](C=O)=[CH:34]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[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([CH2:12][N:13]([CH2:15][C:35]3[C:36]4[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=4)[N:33]([CH3:32])[CH:34]=3)[CH2:14]1)[CH2:10][C:9]2=[O:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 878941-Methyl-1H-indole-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67071422HCID 67071422, compound

Product 1

HCID 67071514HCID 67071514, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (0.11 ml, 0.77 mmol) was added to a suspension of Intermediate 4 (240 mg, 0.77 mmol) in DCM (10 ml). The mixture was stirred at RT for 10 min and then the pH value was adjusted to 5 with AcOH. The mixture was treated with N-methyl-indol-3-carbaldehyde (148 mg, 0.93 mmol) and NaBH(OAc)3 (197 mg, 0.93 mmol) following the procedure described in Example 31, Step A, giving (E)-3-[1′-(1-methyl-1H-indol-3-ylmethyl)-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl]-acrylic acid methyl ester (220 mg) as a light orange oil.

Sources & evidence

ORD record
ord-8e0a8d5e6ad84ac9840bd3d53245846e
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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