Sodium triacetoxyborohydride → Tert-butyl (4-(oxetan-3-yl)morpholin-2-yl)methylcarbamate

HRID 573196Notes

Reaction equation

HRID 573196 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:2]1.[O:16]1[CH2:19][C:18](=O)[CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[O:16]1[CH2:19][CH:18]([N:1]2[CH2:6][CH2:5][O:4][CH:3]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:2]2)[CH2:17]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 19081107tert-Butyl [(morpholin-2-yl)methyl]carbamate

Product 1

HCID 86647912Tert-butyl (4-(oxetan-3-yl)morpholin-2-yl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl morpholin-2-ylmethylcarbamate (0.50 g) in dichloromethane (5 mL) was added oxetan-3-one (0.20 g). After stirring for 5 minutes, sodium triacetoxyborohydride (0.735 g) was added. After stirring for 2 hours, the reaction was diluted with dichloromethane (50 mL) and quenched with saturated NaHCO3 solution (50 mL). The organic layer was separated, washed with brine (40 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 80 g) eluting with a gradient of 0.5% to 5% methanol/dichloromethane over 40 minutes (flow=40 ml/minute) gave the title compound.

Workup

  1. stirringAfter stirring for 2 hours
  2. customquenched with saturated NaHCO3 solution (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (40 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washSilica gel chromatography (Reveleris 80 g) eluting with a gradient of 0.5% to 5% methanol/dichloromethane over 40 minutes (flow=40 ml/minute)

Sources & evidence

ORD record
ord-ba4909475ec24eedaed5a7bbcd0c3789
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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