(R)-N-Boc-2-Hydroxymethylmorpholine Chemical Properties

Melting point:

59-61 °C

Boiling point:

321 °C

Density 

1.118

Flash point:

148 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

14.36±0.10(Predicted)

InChI

InChI=1S/C10H19NO4/c1-10(2,3)15-9(13)11-4-5-14-8(6-11)7-12/h8,12H,4-7H2,1-3H3/t8-/m1/s1

InChIKey

FJYBLMJHXRWDAQ-MRVPVSSYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCO[C@@H](CO)C1

Safety Information

HS Code 

2934999090

(R)-N-Boc-2-Hydroxymethylmorpholine Usage And Synthesis

Uses

(R)-N-Boc-2-hydroxymethylmorpholine is used for preparation of inhibitors of Checkpoint Kinase 1 through template screening.

Synthesis

Intermediate 111 (19.8 g, 64.4 mmol) was stirred and reacted for 16 h under hydrogen atmosphere with 10% Pd/C (1.98 g, 1.86 mmol) as catalyst. Upon completion of the reaction, the catalyst was removed by vacuum filtration and the filtrate was concentrated under reduced pressure to afford 13.98 g (100% yield) of (R)-N-Boc-2-hydroxymethylmorpholine, the product was a colorless viscous oil that crystallized upon standing. The 1H NMR (250 MHz, chloroform-d) data of the product were as follows: δ [ppm] 3.98 - 3.75 (m, 3H), 3.73 - 3.41 (m, 4H), 3.03 - 2.83 (m, 1H), 2.82 - 2.65 (m, 1H), 2.12 (t, J = 5.9 Hz, 1H), 1.45 (s, 9H).

References

[1] Heterocycles, 1993, vol. 35, # 1, p. 105 - 109
[2] Patent: WO2016/91776, 2016, A1. Location in patent: Page/Page column 290
[3] Patent: WO2008/124575, 2008, A1. Location in patent: Page/Page column 112; 113-114
[4] Patent: US2010/184805, 2010, A1. Location in patent: Page/Page column 30-31
[5] Patent: WO2007/70201, 2007, A1. Location in patent: Page/Page column 176

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