Trimethyl orthoformate → HCID 22256511, compound

HRID 351170Notes

Reaction equation

HRID 351170 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.[N+](C1C=CC=CC=1S([N:26]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1)[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[CH:30][CH:29]=1)(=O)=O)([O-])=O.[BH3-][C:44]#[N:45].[Na+].C(OC)(OC)OC>CO.C(O)(=O)C>[N:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[CH2:36][NH:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][N:35]([CH2:28][C:27]2[NH:26][CH:36]=[CH:44][N:45]=2)[CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:10]2)=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 777857-Methoxy-2-tetraloneHCID 5003444Sodium cyanoborohydrideHCID 22708748N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-1,4-benzenedimethanamine

Product 1

HCID 22256511HCID 22256511, compoundYield 183.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

Using general procedure G: Reaction of 7-methoxy-2-tetralone (299 mg, 1.70 mmol) and N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-1,4-benzenedimethanamine (500 mg, 1.21 mmol) with NaBH3CN (296 mg, 4.72 mmol) in a mixture of MeOH (15 mL), trimethyl orthoformate (8.5 mL) and acetic acid (15 drops) for 3.5 hours followed by purification of the crude material by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH 98:1:1) gave the desired product (520 mg, 75%) as a yellow foam.

Workup

  1. customfollowed by purification of the crude material by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH 98:1:1)

Sources & evidence

ORD record
ord-99d6a58f528c474bacb6dec2147f4b2c
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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