Diethyl Ether → tert-Butyl [(3S)-2-oxooxetan-3-yl]carbamate

HRID 631889Notes

Reaction equation

HRID 631889 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:34]([NH:41][C@H:42]([C:45]([OH:47])=[O:46])[CH2:43]O)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].CCOCC>CC#N>[C:37]([O:36][C:34](=[O:35])[NH:41][C@H:42]1[CH2:43][O:47][C:45]1=[O:46])([CH3:38])([CH3:39])[CH3:40]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 14812Phosphorus oxide (P4O10)HCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 2763194tert-Butyl [(3S)-2-oxooxetan-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Conditions

Temperature
-35 °C

Procedure

To a stirred solution of dry PPh3 (72 h under vacuum in the presence of P2O5) (5 mmol) in dry CH3CN (31 mL), kept at −50° C. under N2, dimethylazodicarboxylate (5 mmol) and, after 20 min, a solution of 1 (4.47 mmol) in CH3CN (10.4 mL), were added dropwise. The mixture was stirred for 1.5 h at −50/−35° C. and concentrated. Purification of the residue by flash-chromatography (cyclohexane/EtOAc 8:2 to 6:4) gave crude 2, which was finally washed and triturated to afford a white solid. Mp 120-122° C. (Et2O). [α]D20=−27° (c 0.1, CH3CN). 1H NMR is in accordance with literature (Arnold, et al., 1985).

Workup

  1. custom72 h
  2. customkept at −50° C. under N2
  3. concentrationconcentrated
  4. customPurification of the residue by flash-chromatography (cyclohexane/EtOAc 8:2 to 6:4)
  5. customgave crude 2, which
  6. washwas finally washed
  7. customtriturated
  8. customto afford a white solid

Sources & evidence

ORD record
ord-dfc09636b34e4f0db4867c28ca32bf38
Source dataset
uspto-grants-2016_04
Patent number
US09321743B2

Reaction notes

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