Sodium borohydride → HCID 86587748, compound

HRID 432100Notes

Reaction equation

HRID 432100 reaction equation
[OH:1][C@H:2]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[CH2:3][N:4]([CH2:12][C@H:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([N+:23]([O-])=O)[CH:19]=2)[O:14]1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[BH4-].[Na+]>C1COCC1.C(O)C.[Pd]>[NH2:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[O:14][C@@H:13]([CH2:12][N:4]([CH2:3][C@H:2]([OH:1])[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:22][CH2:21]2

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86587747HCID 86587747, compound

Product 1

HCID 86587748HCID 86587748, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (2R)-2-hydroxy-2-(3-pyridinyl)ethyl{[(2R)-6-nitro-3,4-dihydro-2H-chromen-2-yl]methyl}carbamate (Example 171, 500 mg, 1.2 mmol) was dissolved in degassed THF, and to the solution was added Pd/C (50 mg, 10%) under argon and cooled to 0° C. NaBH4 was dissolved in ethanol and added to the reaction slowly to avoid excessive bubbling. After gas evolution had stopped, the reaction was warmed to room temperature and monitored by TLC. When complete, the reaction was cooled to 0° C. and quenched by the addition of ice. The black precipitate was then filtered through Celite® and the filtrate was concentrated in vacuo until cloudy. The filtrate was then extracted with ethyl acetate and the crude material was purified via flash chromatography to yield the product (30%). 1H NMR (DMSO-d6, δ): 8.4 (m, 2H), 7.7 (m, 1H), 7.4 (m, 1H), 6.4 (d, 1H), 6.3 (s, 1H), 6.2 (d, 1H), 5.6 (d, 1H), 4.8 (m, 1H), 4.5 (m, 1H), 3.5 (m, 2H), 3.4 (m, 2H), 2.8 (m, 2H), 1.8 (m, 1H), 1.5 (m, 1H), 1.2 (d, 9H); LC/MS: m/z 399, MH+ 400

Workup

  1. additionadded to the reaction slowly
  2. temperaturethe reaction was warmed to room temperature
  3. temperatureWhen complete, the reaction was cooled to 0° C.
  4. customquenched by the addition of ice
  5. filtrationThe black precipitate was then filtered through Celite®
  6. concentrationthe filtrate was concentrated in vacuo until cloudy
  7. extractionThe filtrate was then extracted with ethyl acetate
  8. customthe crude material was purified via flash chromatography

Sources & evidence

ORD record
ord-6c8a93e9bab94628a9e8fdce2cbe4c08
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Reaction notes

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