Hydrochloric Acid → HCID 19906372, compound

HRID 2371812Notes

Reaction equation

HRID 2371812 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH2:15][CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([NH:25]C(=O)C(F)(F)F)[CH:23]=2)[CH:18]=[CH:17]1)[C:8]([O:10][CH3:11])=[O:9].O1CCCC1.[ClH:37]>CO>[ClH:37].[NH2:25][C:22]1[CH:23]=[C:24]2[C:19]([CH2:18][CH:17]=[C:16]2[CH2:15][C:14]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=2[O:4][CH3:3])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 19906418HCID 19906418, compound

Product 1

HCID 19906372HCID 19906372, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.24 g), was added to a 0° C. mixture of methyl 3-methoxy-4-[6-(trifluoroacetamido)-1H-inden-1-ylmethyl]benzoate (1.25 g), tetrahydrofuran (14 ml) and methanol (2 ml). After 15 min, the reaction was stirred at room temperature for 2 h and cooled to 0° C. 1N Hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed (sodium bicarbonate, water, brine) and dried (MgSO4). Evaporation, dissolution in ether (50 ml) and addition of ethereal hydrogen chloride (5 ml) afforded methyl 4-(6-amino-3H-inden-1-ylmethyl)-3-methyoxybenzoate hydrochloride (0.85 g, 79%) as a colorless solid; mp 213.0°-215.0° C.; MS(CI), m/e=310 (M+H).

Workup

  1. temperaturecooled to 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed (sodium bicarbonate, water, brine)
  4. dry with materialdried (MgSO4)
  5. customEvaporation, dissolution in ether (50 ml)
  6. additionaddition of ethereal hydrogen chloride (5 ml)

Sources & evidence

ORD record
ord-717cd2045f71483f867ac967b10ed961
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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