Hydrochloric Acid → (2R,3R,4S,5S,6R)-2-[3-[[4-(3-benzyloxypropoxy)phenyl]-hydroxy-methyl]-4-methyl-indol-1-yl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

HRID 2284863Notes

Reaction equation

HRID 2284863 reaction equation
C([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12]C(=O)C)[C@H:10]([O:16]C(=O)C)[C@@H:9]([O:20]C(=O)C)[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([C:34](=[O:53])[C:35]3[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH2:44][O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[CH:37][CH:36]=3)=[CH:25]2)[O:7]1)(=O)C.C1COCC1.[BH4-].[Na+].Cl>O.ClCCl.C(O)C>[CH2:46]([O:45][CH2:44][CH2:43][CH2:42][O:41][C:38]1[CH:37]=[CH:36][C:35]([CH:34]([OH:53])[C:26]2[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])[N:24]([C@H:8]3[C@H:9]([OH:20])[C@@H:10]([OH:16])[C@H:11]([OH:12])[C@@H:6]([CH2:5][OH:4])[O:7]3)[CH:25]=2)=[CH:40][CH:39]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 118045136[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[4-(3-benzyloxypropoxy)benzoyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate

Product 1

HCID 118045132(2R,3R,4S,5S,6R)-2-[3-[[4-(3-benzyloxypropoxy)phenyl]-hydroxy-methyl]-4-methyl-indol-1-yl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 0.5 L stirred round bottom flask, purged with nitrogen, charge [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[4-(3-benzyloxypropoxy)benzoyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (12.33 mmol), THF (50 mL), and ethanol (100 mL). Add sodium tetrahydroborate (37.0 mmol) and stir at room temperature for 6 hours. Acidify by dropwise addition of 5N HCl then dilute with water (200 mL) and dichloromethane (200 mL). Separate the organics and wash with brine (200 mL). Dry over sodium sulphate, filter, and concentrate to give the title compound as a mixture of diastereomers in sufficient purity to be used without further purification in the next step (7.2 g crude) mass spectrum (m/z): 546.4 (M+1-18).

Workup

  1. custompurged with nitrogen
  2. customSeparate the organics and
  3. washwash with brine (200 mL)
  4. dry with materialDry over sodium sulphate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-375793dcd5524b84906949b2378eae97
Source dataset
uspto-grants-2015_09
Patent number
US09145437B2

Reaction notes

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