(1R,2S)-(+)-cis-1-Amino-2-indanol → HCID 66608540, compound

HRID 456236Notes

Reaction equation

HRID 456236 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH:23]=O)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[CH2:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C@@H:28]([NH2:35])[C@H:27]1[OH:36].C([BH3-])#N.[Na+]>C(O)(=O)C.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][C:14]=2[CH2:23][NH:35][C@@H:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:26][C@@H:27]2[OH:36])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 5003444Sodium cyanoborohydrideHCID 86633167(2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 66608540HCID 66608540, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

(2′-Formyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.153 g, 0.43 mmol), (1R,2S)-(+)-cis-1-amino-2-indanol (0.065 g, 0.43 mmol), sodium cyanoborohydride (0.041 g, 0.65 mmol), and acetic acid (3 drops) were combined in CH2Cl2 (1.5 mL), and the reaction was stirred for 30 minutes at room temperature. The mixture was diluted with CH2Cl2 and saturated aqueous NaHCO3, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d5a8c9efb34e44198a80d5ce0be82b85
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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