Lithium borohydride → HCID 86591375, compound

HRID 722141Notes

Reaction equation

HRID 722141 reaction equation
[BH4-].[Li+].C([O:5][C:6](=O)[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:18](=[CH:19][CH:20]=1)[CH2:17][CH:16]1[CH:21]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:13]([CH2:14][CH2:15]1)[CH2:12]2)C>C1COCC1>[C:26]([O:25][C:23](=[O:24])[NH:22][CH:21]1[CH:16]2[CH2:15][CH2:14][CH:13]1[CH2:12][C:11]1[C:18]([CH2:17]2)=[CH:19][CH:20]=[C:9]([O:8][CH2:7][CH2:6][OH:5])[CH:10]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 69666276HCID 69666276, compound

Product 1

HCID 86591375HCID 86591375, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (56 mg) was added in a single portion to a stirred solution of the product from Step 2 (1.0 g) in dry THF. (20 mL). The resulting solution was stirred at room temperature for 18 hrs, quenched with NH4Cl (aq. satd 50 mL) and extracted into DCM. The organic extract was dried over MgSO4, filtered and the solvent removed under reduced pressure and the product purified by flash chromatography over silica (200–400 mesh, 10–60% EtOAc/isohexane) to give [5-(2-hydroxy-ethoxy)tricyclo [8.2.1.03,8]trideca-3,5,7-trien-13-yl]-carbamic acid tert-butyl ester as a white solid (340 mg). 1H NMR (CDCl3 400 MHz), δ 1.20 (2H, m), 1.47 (9H, s), 1.69 (2H, m), 2.04 (1H, m), 2.50 (4H, m), 2.96 (2H, m), 3.94 (2H, m), 4.05 (3H, m), 4.99 (1H, brm), 6.62 (1H, dd, J=8.0, 1.0 Hz), 6.67 (1H, d, J=1.0 Hz), 6.98 (1H, d, J=8.0 Hz).

Workup

  1. customquenched with NH4Cl (aq. satd 50 mL)
  2. extractionextracted into DCM
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customthe product purified by flash chromatography over silica (200–400 mesh, 10–60% EtOAc/isohexane)

Sources & evidence

ORD record
ord-f23552d9e5114317b2375184bbd0a9ea
Source dataset
uspto-grants-2006_11
Patent number
US07138400B2

Reaction notes

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