Trimethyl orthoformate → HCID 57948569, compound

HRID 2035407Notes

Reaction equation

HRID 2035407 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1.[OH-].[Na+].COC(OC)OC.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][O:27][C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[CH:34]=[C:33]([CH:38]=O)[CH2:32][CH2:31]3)=[CH:20][CH:19]=1.[BH4-].[Na+].Cl.C(OCC)(=O)C>CO.O1CCCC1>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][O:27][C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[CH:34]=[C:33]([CH2:38][N:1]2[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]2)[CH2:32][CH2:31]3)=[CH:22][CH:23]=1

Participants

9

Reactant 6

HCID 9005Trimethyl orthoformateHCID 14798Sodium HydroxideHCID 931923-azetidinecarboxylic AcidHCID 4311764Sodium borohydrideHCID 21866389Hydrogen chloride-ethyl acetateHCID 86635605HCID 86635605, compound

Product 1

HCID 57948569HCID 57948569, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Azetidine-3-carboxylic acid (46 mg) and sodium hydroxide (18 mg) were dissolved in methanol (4 mL). To this solution, trimethoxymethane (0.050 mL) and a tetrahydrofuran (1 mL)-methanol (1 mL) mixed solution of 6-[3-(4-chlorophenyl)propoxy]-3,4-dihydronaphthalene-2-carboaldehyde (100 mg) were successively added under ice cooling. The reaction mixture was stirred for 3.5 hours under ice cooling. To the reaction mixture, sodium borohydride (17 mg) was added under ice cooling. The reaction mixture was stirred under ice cooling for 20 minutes. Thereafter, 4 mol/L hydrogen chloride/ethyl acetate solution was added until it was neutral, and concentrated. The obtained residue was purified by flash silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:10:1 to 80:20:4), to thereby obtain the title compound (79 mg) having the following physical properties.

Workup

  1. additionwere successively added under ice cooling
  2. stirringThe reaction mixture was stirred under ice cooling for 20 minutes
  3. concentrationconcentrated
  4. customThe obtained residue was purified by flash silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:10:1 to 80:20:4)

Sources & evidence

ORD record
ord-b55a0149377a400b805fe94abbc0afce
Source dataset
uspto-grants-2013_11
Patent number
US08575134B2

Reaction notes

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