Water → Tert-butyl 4-(cyclopropylmethyl)piperazine-1-carboxylate

HRID 1272034Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[CH:15]([CH:17]1[CH2:19][CH2:18]1)=O.C([BH3-])#N.[Na+]>C1COCC1.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:15][CH:17]2[CH2:19][CH2:18]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 1-tert-butyloxycarbonylpiperazine (2.24 g, 12.0 mmol) in THF (10 ml) were added water (0.15 ml), acetic acid (3.60 ml), formylcyclopropane (1.35 ml, 18.1 mmol), and sodium cyanoborohydride (18 ml of a 1M solution in THF, 18 mmol). The mixture was stirred at 20° C. for 14 hours. The mixture is concentrated under reduced pressure, and the residue is mixed with water (80 ml) and 1 N aqueous hydrochloric acid (40 ml). After washing with ethyl acetate (20 ml) the aqueous phase is made basic by addition of potassium carbonate (approx. 20 g) and extracted with ethyl acetate (4×30 ml). The combined extracts were dried with magnesium sulphate and concentrated under reduced pressure, to yield 2.3 g (80%) of the title compound as a colourless oil.

Workup

concentrationThe mixture is concentrated under reduced pressure
additionthe residue is mixed with water (80 ml) and 1 N aqueous hydrochloric acid (40 ml)
washAfter washing with ethyl acetate (20 ml) the aqueous phase
additionis made basic by addition of potassium carbonate (approx. 20 g)
extractionextracted with ethyl acetate (4×30 ml)
dry with materialThe combined extracts were dried with magnesium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1b2cf58e29594705bc4b774e43aa8ac0
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208497B2

Reaction notes

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