Hydrochloric Acid → {(S)-6-[(R)-4-bromo-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 2170934Notes

Reaction equation

HRID 2170934 reaction equation
N1CCOC[CH2:2]1.[Br:7][C:8]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]2[C:9]=1[CH2:10][CH2:11][C@H:12]2[O:18][C:19]1[CH:31]=[CH:30][C:22]2[C@H:23]([CH2:26][C:27]([OH:29])=[O:28])[CH2:24][O:25][C:21]=2[CH:20]=1.Cl>CO>[CH3:2][O:28][C:27](=[O:29])[CH2:26][C@H:23]1[C:22]2[CH:30]=[CH:31][C:19]([O:18][C@H:12]3[C:13]4[C:9](=[C:8]([Br:7])[CH:16]=[CH:15][C:14]=4[F:17])[CH2:10][CH2:11]3)=[CH:20][C:21]=2[O:25][CH2:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117965907HCID 117965907, compound

Product 1

HCID 86697103{(S)-6-[(R)-4-bromo-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.87 g (11.9 mmol) [(S)-6-((R)-4-bromo-7-fluoroindan-1-yloxy)-2,3-dihydrobenzo-furan-3-yl]-acetic acid morpholine salt is suspended in 22 ml MeOH. Then, 3.56 ml (14.2 mmol) HCl (4 M in dioxane) is added and the funnel is rinsed with 1.50 ml MeOH. The mixture is stirred overnight at r.t. and seeds are added. After 30 min, 5.90 ml water is added and stirring is continued. The precipitated product is filtered off, washed with 14.6 ml MeOH/water (4:1) and dried. Yield: 4.25 g; Rf=0.39 (silica gel, PE/EtOAc=8/2); Mass spectrum (ESI): m/z=421 [M+H]+.

Workup

  1. washthe funnel is rinsed with 1.50 ml MeOH
  2. additionseeds are added
  3. waitAfter 30 min
  4. addition5.90 ml water is added
  5. stirringstirring
  6. filtrationThe precipitated product is filtered off
  7. washwashed with 14.6 ml MeOH/water (4:1)
  8. customdried

Sources & evidence

ORD record
ord-26804141a09f4c979420231cff76df83
Source dataset
uspto-grants-2015_06
Patent number
US09051289B2

Reaction notes

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