Trimethyl orthoformate → HCID 9886548, compound

HRID 351169Notes

Reaction equation

HRID 351169 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7][CH2:6]2.[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#N.[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][NH:35][CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 5003444Sodium cyanoborohydrideHCID 22708748N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-1,4-benzenedimethanamine

Product 1

HCID 9886548HCID 9886548, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

Using General Procedure G: 6-methoxy-2-tetralone (112 mg, 0.63 mmol), N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-1,4-benzenedimethanamine (186 mg, 0.45 mmol) and NaBH3CN (110 mg, 1.76 mmol) in a mixture of MeOH (5 mL), trimethyl orthoformate (2.8 mL) and acetic acid (5 drops) were reacted for 3.5 hours. Purification of the crude material by chromatography on silica gel (CH2Cl2/MeOH/NH4OH 98:1:1) gave the desired product (102 mg, 40%) as a yellow foam.

Workup

  1. customwere reacted for 3.5 hours
  2. customPurification of the crude material by chromatography on silica gel (CH2Cl2/MeOH/NH4OH 98:1:1)

Sources & evidence

ORD record
ord-f0f92533e2e543a1b40c3d59cb6796ef
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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