Nitrogen → HCID 13553301, compound

HRID 622717Notes

Reaction equation

HRID 622717 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2/[CH:16]=[CH:17]/[C:18](=[O:27])[CH2:19][CH:20]([OH:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:4][C:3]=1[CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].C(B(CC)CC)C.N#N.[BH4-].[Na+]>C1COCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2/[CH:16]=[CH:17]/[CH:18]([OH:27])[CH2:19][CH:20]([OH:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:4][C:3]=1[CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 947NitrogenHCID 7357TriethylboraneHCID 4311764Sodium borohydrideHCID 14750004HCID 14750004, compound

Product 1

HCID 13553301HCID 13553301, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

The compound (1g) (1.0 g, 1.96 mmol) was dissolved in dry THF (5 mL) under N2 and then treated with triethylborane (1 M in THF, 2.9 mL, 2.9 mmol). After aging for 5 minutes, the reaction mixture was cooled to -98° C. (MeOH-liq. N2 bath). Sodium borohydride (85 mg, 2.25 mmol) was added followed by MeOH (2 mL) over 5 minutes. After stirring for an additional 0.5 hours, the reaction mixture was allowed to warm to -60° C. and then was quenched by the careful addition of 30% H2O2 (4 mL) in H2O (10 mL). The mixture was stirred vigourously at ambient temperature for 0.5 hours and then distributed between 1 N HCl (50 mL) and EtOAc (100 mL). The organic layer was washed with H2O (2×50 mL), dried, filtered and evaporated to provide the compound (1h) as a pale yellow gum. 1H NMR shows an 11:1 ratio of erythro vs threo; NMR 0.12 (6 H, s), 0.93 (9 H, s), 1.42-1.61 (2 H, m), 2.32 (6 H, s), 2.34-2.46 (2 H, m), 3.70 (3 H, s), 4.05-4.15 (H, m), 4.3-4.4 (H, m), 4.7-4.85 (2 H, m), 5.29 (H, dd, J=7 and 16 Hz), 6.43 (H, d, J=16 Hz), and 6.50 (H, d, J=16 Hz).

Workup

  1. customwas quenched by the careful addition of 30% H2O2 (4 mL) in H2O (10 mL)
  2. stirringThe mixture was stirred vigourously at ambient temperature for 0.5 hours
  3. washThe organic layer was washed with H2O (2×50 mL)
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4f4979db1655406ca1e40b1a981c0c88
Source dataset
uspto-grants-1988_09
Patent number
US04772626

Reaction notes

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