Acetyl chloride → 5-(3-Hydroxymethylphenyl)-3-(pyrrolidin-2(R)-ylmethyl)-1H-indole

HRID 1441057Notes

Reaction equation

HRID 1441057 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][OH:33])[CH:27]=3)[CH:24]=2)[NH:19][CH:18]=1)=O)C1C=CC=CC=1.C(Cl)(=O)C>C(O)C>[OH:33][CH2:32][C:28]1[CH:27]=[C:26]([C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[C:17]3[CH2:16][C@H:12]2[CH2:13][CH2:14][CH2:15][NH:11]2)[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 228595573-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-(3-hydroxymethylphenyl)-1H-indole

Product 1

HCID 228595715-(3-Hydroxymethylphenyl)-3-(pyrrolidin-2(R)-ylmethyl)-1H-indoleYield 63.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-(3-hydroxymethylphenyl)-1H-indole (1.030 g, 2.316 mmol) (see Preparation 38) in ethanol was reduced using catalytic hydrogenation as described in Example 35 except that no acetyl chloride was used in the reaction. This gave the title compound as an off-white foam (453 mg). Found: C,72.36; H,6.76; N,8.20; C20H22N2O.3/8CH2Cl2 requires: C,72.35; H,6.78; N,8.28%.

Workup

  1. customwas used in the reaction

Sources & evidence

ORD record
ord-afce1b3ef86445f4bfb4527c9be018b1
Source dataset
uspto-grants-1996_03
Patent number
US05502065

Reaction notes

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