Lithium borohydride → HCID 22319460, compound

HRID 24058Notes

Reaction equation

HRID 24058 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][C:10]2[CH:14]=[CH:15][C:16]([CH2:18][C:19](OC(C)(C)C)=[O:20])=[N:17][C:9]1=2)=O)(C)(C)C.[BH4-].[Li+]>C1COCC1>[O:11]1[CH2:12][CH2:13][NH:8][C:9]2[N:17]=[C:16]([CH2:18][CH2:19][OH:20])[CH:15]=[CH:14][C:10]1=2

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 668193646-Tert-butoxycarbonylmethyl-2,3-dihydro-pyrido[3,2-b][1,4]oxazine-4-carboxylic acid tert-butyl ester

Product 1

HCID 22319460HCID 22319460, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-tert-butoxycarbonylmethyl-2,3-dihydro-pyrido[3,2-b][1,4]oxazine-4-carboxylic acid tert-butyl ester (350 mg, 1mmol) in THF (4.0 ml) was added a solution of lithium borohydride (0.6 ml, 2.0 m in thf). The mixture was refluxed overnight, then cooled in an ice-bath. Aqueous solution of naoh (0.36 ml, 5%) was added. The ice-bath was removed. Additional h2o (0.36 ml) was added and the mixture stirred for 10 min. Celite and na2so4 were added. The mixture was filtered through celite, and the celite washed with etoac. The filtrate and washing were combined, dried over na2so4, concentrated, and flash chromatographed on silica gel, eluting with meoh/dcm (1, 2, 3, 4%) to give the product (171 mg, 94% yield) as a yellow oil. 1H NMR (CDCl3) δ 6.90 (d, 1H, J=7.8 Hz), 6.39 (d, 1H, J=7.7 Hz), 4.85 (bs, 1H), 4.20 (t, 2H, J=4.4 Hz), 3.91 (t, 2H, J=5.5 Hz), 3.69-3.52 (m, 2H), 2.78 (t, 2H, J=5.6 Hz).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperaturecooled in an ice-bath
  3. additionAqueous solution of naoh (0.36 ml, 5%) was added
  4. customThe ice-bath was removed
  5. additionAdditional h2o (0.36 ml) was added
  6. additionCelite and na2so4 were added
  7. filtrationThe mixture was filtered through celite
  8. washthe celite washed with etoac
  9. washThe filtrate and washing
  10. customdried over na2so4
  11. concentrationconcentrated
  12. customflash chromatographed on silica gel
  13. washeluting with meoh/dcm (1, 2, 3, 4%)

Sources & evidence

ORD record
ord-bdd2f6796bb1417c8087d64887f537bd
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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