Acetic Acid → HCID 67071731, compound

HRID 874326Notes

Reaction equation

HRID 874326 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].CC(O)=O.[CH3:34][N:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37](C=O)=[CH:36]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[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]([CH2:17][C:37]3[C:38]4[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=4)[N:35]([CH3:34])[CH:36]=3)[CH2:12]1)[CH2:10][C:9]2=[O:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 878941-Methyl-1H-indole-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67071461HCID 67071461, compound

Product 1

HCID 67071731HCID 67071731, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (0.14 ml, 1.0 mmol) was added to suspension of Intermediate 2 (290 mg, 0.86 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 (164 mg, 1.03 mmol) and NaBH(OAc)3 (219 mg, 1.03 mmol) following the procedure described in Example 31, A, giving (E)-3-[1′-(1-methyl-1H-indol-3-ylmethyl)-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (380 mg) as a light orange solid.

Sources & evidence

ORD record
ord-0748f578b0244a4ebd892389835ff3d5
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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