Hydrochloric Acid → {(S)-6-[(R)-4-(8-Oxa-3-aza-bicyclo[3.2.1]oct-3-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422628Notes

Reaction equation

HRID 1422628 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH:28]=O)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.Cl.[CH:32]12[O:39][CH:36]([CH2:37][CH2:38]1)[CH2:35][NH:34][CH2:33]2.C([O-])(=O)C.[Na+].Cl.C([O-])([O-])=O.[K+].[K+]>O.ClCCCl>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH2:28][N:34]5[CH2:33][CH:32]6[O:39][CH:36]([CH2:37][CH2:38]6)[CH2:35]5)[C:20]([C:24]([F:27])([F:25])[F:26])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 517045Sodium AcetateHCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochlorideHCID 86700810{(S)-6-[(R)-4-Formyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 90313422{(S)-6-[(R)-4-(8-Oxa-3-aza-bicyclo[3.2.1]oct-3-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

NaHB(O2CCH3)3 (30 mg) is added to a mixture of {(S)-6-[(R)-4-formyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (20 mg), 8-oxa-3-aza-bicyclo[3.2.1]octane hydrochloride (14 mg), sodium acetate (4 mg), and 1,2-dichloroethane (1 mL) at room temperature. The mixture is stirred at room temperature overnight. 1 M aqueous HCl solution is added, the resulting mixture is stirred for 10 min, and then water is added. The mixture is basified with aqueous K2CO3 solution and extracted with ethyl acetate. The combined extract is washed with brine, dried (Na2SO4), and concentrated to give the title compound. LC (method 4): tR=1.15 min; Mass spectrum (ESI+): m/z=518 [M+H]+.

Workup

  1. stirringthe resulting mixture is stirred for 10 min
  2. extractionextracted with ethyl acetate
  3. extractionThe combined extract
  4. washis washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1788c48b97ab487c88adc49a20bc8ac0
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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