Dichloromethane → HCID 57871401, compound

HRID 550222Notes

Reaction equation

HRID 550222 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH2:34][CH3:35])[C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([CH3:36])[CH:21]=3)([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:11]=2)[CH:6]=1)=[O:4].[BH4-].[Na+].C(Cl)Cl.CCOC(C)=O.C(Cl)Cl>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([CH2:16][CH3:17])([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH2:34][CH3:35])[CH:28]([OH:33])[C:29]([CH3:30])([CH3:31])[CH3:32])=[C:22]([CH3:36])[CH:21]=3)[CH2:18][CH3:19])[CH:11]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 21226138Dichloromethane ethylacetateHCID 57871402HCID 57871402, compound

Product 1

HCID 57871401HCID 57871401, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described in Example 2; treat 6-{1-[4-(3,3-dimethyl-1-ethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}naphthalene-2-carboxylic acid methyl ester with NaBH4 in THF at 0 C. Chromatograph the residue (CH2Cl2 to 2% EtOAc/CH2Cl2) to give diastereomeric isomer pair 1 of the title compound as a glassy foam (1.004 g, 77%) and diastereomeric isomer pair 2 of the title compound as a glassy foam (102 mg, 8%).

Sources & evidence

ORD record
ord-63fe3a7be03e4497b572418d51b72d9c
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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