Sodium borohydride → HCID 67229292, compound

HRID 1844320Notes

Reaction equation

HRID 1844320 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]([C@@:17]1([C:37]2([OH:41])[CH2:40][CH2:39][CH2:38]2)[CH2:21][CH2:20][C@@H:19]([N:22](C(=O)C(F)(F)F)[C@@H:23]2[C@H:28]([O:29][CH3:30])[CH2:27][O:26][CH2:25][CH2:24]2)[CH2:18]1)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]([C@@:17]1([C:37]2([OH:41])[CH2:40][CH2:39][CH2:38]2)[CH2:21][CH2:20][C@@H:19]([NH:22][C@@H:23]2[C@H:28]([O:29][CH3:30])[CH2:27][O:26][CH2:25][CH2:24]2)[CH2:18]1)=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86654423HCID 86654423, compound

Product 1

HCID 67229292HCID 67229292, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.31 g (2.23 mmol) of 1,5-anhydro-3-{[(1R,3S)-3-{[(1S,4S)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}-3-(1-hydroxycyclobutyl)cyclopentyl](trifluoroacetyl)amino}-2,3-dideoxy-4-O-methyl-D-erythro-pentitol and 860 mg (23 mmol) of sodium borohydride 6.3 mL of ethanol was stirred at ambient temperature for 18 h, then partitioned between water and dichloromethane. The aqueous phase was extracted with additional dichloromethane, and the combined organic phase dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography on silica using 6-15% methanol in dichloromethane afforded 1.08 g (98%) of the title compound as a white foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.42-1.47 (m, 9H) 1.56-2.35 (m, 14H) 2.72 (br. s., 1H) 3.11-3.68 (m, 10H) 3.90-3.98 (m, 1H) 4.08 (dd, J=12.6, 2.7 Hz, 1H) 4.38-4.58 (m, 1H) 4.84-5.16 (m, 1H). LC-MS ES+ 494.3. HRMS calculated for C26H43N3O6: 494.3230. found: 494.3260.

Workup

  1. custompartitioned between water and dichloromethane
  2. extractionThe aqueous phase was extracted with additional dichloromethane
  3. dry with materialthe combined organic phase dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c95af676cb28412db6906e7db6a2b6d5
Source dataset
uspto-grants-2015_02
Patent number
US08946413B2

Reaction notes

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